Fructopyranosyl fluoride

The 2,5-anhydrides of 2-ketoses constitute a special case, in which the hemiacetalic carbon atom is involved in the anhydride bridge. Such anhydrides more closely resemble the 1,6-anhydroaldoses (glycosans) than the 2,5-anhydroaldoses. An example of a 2,5-anhydride of a 2-hexulose is obtained by the action of base on a D-fructosyl fluoride derivative treatment of l-0-methyl-/3-D-fructopyranosyl fluoride at 90° with concentrated, aqueous sodium hydroxide leads,80 in poor yield, to 2,5-anhydro-l-0-methyl-/3-D-fructopyranose. 

In acid solution, l-deoxy-o-tAreo-pentulose forms the dimeric 24, and the stereoselective synthesis of di-P-D-fructopyranose 1,2 2,1 -dianhydride has been achieved by way of a fructopyranosyl fluoride. The Michael addition of thiols, alcohols and C-nucleophiles to levoglucosenone has been used in the synthesis of analogues of the herbicide l,6-anhydro-4-0-benzyl-3-deoxy-2-( >-methyl-P-D-ri o-hexopyranose. ... 

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